Skateboarding has been a very popular activity for a number of years. In addition to simply riding on a skateboard, however, many skateboarders now try to perform complex tricks, which have become more and more difficult as each new generation of skateboarders tries to outdo the last. Many skateboarding tricks require the skateboarder to flip or otherwise reposition the skateboard using his or her feet. For example, at the apex of a jump, a skateboarder might use his or her foot to flip the skateboard so that it rotates 360°, but still lands on its wheels so that the skateboarder can, in turn, land on the skateboard at the end of the jump. Typically, the skateboarder will use the top surface of his or her shoe to “grab” the underside of the skateboard in order to flip it. While this type of trick would be difficult under any circumstances, the skateboarder's footwear can make this type of trick even more difficult. For example, if the footwear has a smooth upper surface, this surface may not provide enough friction to allow the skateboarder to successfully grab the skateboard. Accordingly, it would be desirable to provide footwear for use with skateboarding that allows the skateboarder to more securely and better control flipping or other movement of the skateboard with his or her foot.